α-Fluorination of 6-phenylsulfinyl-2-azabicyclo[2.2.1]Heptan-3-one and synthesis of 2'-fluoro substituted carbovir

Tetrahedron Letters

Volumn 39, Issue 26, 1998, Pages 4687-4690

  Toyota, Akemi ^a   Nishimura, Akiko ^a   Kaneko, Chikara ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOVIR;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; FLUORINATION; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS INFECTION;

EID: 0032565848     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00878-8     Document Type: Article

References (16)

1. 1. Vince, R.; Brownell, J. Biochem. Biophys. Res. Commun. 1990, 168, 912.; Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17; Martinez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963-7966.
2. 1. Vince, R.; Brownell, J. Biochem. Biophys. Res. Commun. 1990, 168, 912.; Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17; Martinez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963-7966.
3. 1. Vince, R.; Brownell, J. Biochem. Biophys. Res. Commun. 1990, 168, 912.; Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17; Martinez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963-7966.
4. 2. Toyota, A.; Nishimura, A.; Kaneko, C. Heterocycles 1997, 45, 2105-2108.
5. 3. Toyota, A.; Ono, Y.; Kaneko, C. Tetrahedron Lett. 1995, 36, 6123-6126.
6. 4. Toyota, A.; Ono, Y.; Chiba, J; Sugihara T.; Kaneko, C. Chem. Pharm. Bull. 1996, 44, 703-708.
7. 5. Toyota, A.; Ono, Y.; Kaneko, C.; Hayakawa, I. Tetrahedron Lett. 1996, 37, 8507-8510.
8. 6. Palmer, C. F.; Parry, K. P.; Roberts S. M.; Sik, V. J. Chem. Soc. Perkin Trans. 1 1992, 1021-1028.
9. 2) Since the d-orbital of S atom has much smaller amplitude than that of the Se atom, the corresponding interaction (leading to the endo product) would not be expected in the present reaction.
10. 1-H), 7.68 (3H, m, Ph-H × 3), 8.09 (2H, m, Ph-H × 2).
11. 1-H), 7.70 (3H, m, Ph-H × 3), 7.99 (2H, m, Ph-H × 2).
12. 1-H), 7.69 (3H, m, Ph-H × 3), 7.96 (2H, m, Ph-H × 2).
13. 11. Toyota, A.; Habutani, C.; Katagiri, N.; Kaneko, C. Tetrahedron Lett. 1994, 35, 5665-5668.
14. 12. Lee, G. H.; Choi E. B.; Lee, E.; Pak, C. S. Tetrahedron Lett. 1993, 34, 4541-4542.
15. 13. Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589-592.
16. 8-H).